When you dream of Oahu, whether you’ve been here before or not, you probably close your eyes and picture the waves of North Shore. A lei-covered luau. Maybe a sunset on Waikiki Beach. The pineapple whip at the Dole Plantation. Perhaps the calm beaches of Kailua.

One area you might not think to explore? Oahu’s equal parts trendy and gritty, modern and historic Downtown.

On previous trips to Oahu, I’d spent some brief time Downtown exploring the nightlife in buzzy Chinatown and the Honolulu Museum of Art’s monthly party, Art After Dark. Knowing that this area was right up Ian’s alley, this trip, we were determined to go deeper.

We kicked off our day Downtown with the much-raved about WWII Red Light Tour by Honolulu Exposed. We met bright and early at the Hawaii Theater, where I promptly fell head-over-flip flops with the art deco marquee. Future trip goal: see a show inside!

Our guide and tour founder Carter charmed us in seconds upon meeting — she’d been living in Seattle running a tour company called Seattle Exposed when she became fascinated by Oahu’s Chinatown. Sensing there were stories there just begging to be told, she moved to the island and after months of meticulous research, started sharing them with anyone who would listen. What emerged was a fascinating tour about, as Carter puts it, “sauced sailors, corrupt cops, and purchased pleasure in WWII Honolulu.”

Some visitors to modern Hawaii may be scandalized to know there’s a long history of red light districts on the island. A disproportionate number of men on the island thanks to plantation labor and then later an influx of military personnel created a market for female companionship — I did a double take when Carter said her research led her to believe that during WWII, men outnumbered women in Honolulu 375 to one.

Over the next ninety minutes, we strolled through about a mile of Chinatown and took in dozens of its myths, controversies, scandals, and true stories. Today, Chinatown is rife with craft cocktail bars and popular with nearby University students, but once upon a time, it was a rough area frequented almost exclusively by rowdy sailors on shore leave, and the industries that popped up to entertain them.

The women that flocked to Chinatown to work in brothels known as “boogie houses” were mostly from California, and in most cases their families back on the mainland had no idea what they were really doing for work. They’d write home saying they’d married prominent military officers, and in a few years, after amassing small fortunes, they’d move home playing a grieving — and wealthy — widow.

Their lives on Oahu were no vacation, though. Prostitution was legal in that area, but it was very, very strictly regulated — a crazy list of rules Carter read from barred women working as prostitutes from swimming at Waikiki Beach, going to golf courses, attending dances, going to bars or cafes, owning cars or property, having boyfriends, marrying into the army, wiring money to or telephoning the mainland without permission, going out past 10:30pm, or even riding a bicycle.

A Chinatown prostitute could earn up to $25,000 a year, which when adjusted for inflation is nearly half a million dollars today! Both out of a sense of patriotic investment in the war and to protect their earnings from corrupt police, prostitutes invested thousands in war bonds. They also, in what was my favorite story from the tour, came together after the Pearl Harbor attacks, offering shelter and comfort to soldiers turned away from overcrowded hospitals and nursing them back to health until they could be admitted.

Carter carries photos of some of the real people she discusses, as well as buildings the way they looked in the WWII era — many have not changed much from how they look today! History buffs may have already heard of names like Jean O’Hara, who’s memoir about her life in a Honolulu brothel eventually led to a complete shutdown of the corrupt industry, or Sailor Jerry, who’s historic tattoo shop you’ll visit on the tour.

Carter is truly gifted as a guide — her tour is funny and touching, and compassionate and respectful to her subject matter, people that Hawaii history sometimes tries to brush aside. This tour doesn’t romanticize the realities of sex work — I alternated between wincing at the realities of life in a “boogie house” and admiration for the wits shown by the women highlighted on this tour — nor villainize the sailors who were their enthusiastic customers. It just tells the story of real people doing their best to survive and thrive through one of history’s great tragic wars.

The WWII Red Light District Tour starts most Thursdays through Mondays at 9:30am, but Carter is enthusiastic and flexible, so just give her a holler if that doesn’t fit your schedule. At $30, it’s a literal steal for a morning’s entertainment on Oahu. But clearly, as Carter warns on her website, this tour isn’t for everyone — after all, “f-bombs do fly.”

Since we visited, she’s also developed a Devil’s Den Tour, runs a Chinatown Scavenger Hunt, and soon, will launch a tour dedicated to Hawaii’s final chiefess, Queen Lili`uokalani (I’m dying to come back for that one!) For history buffs and Hawaii enthusiasts alike, these tours are a must.

After such a fascinating deep dive into Chinatown’s rich history, we were raring to explore its vibrant present. With all the gems Carter pointed out along the tour, you’re going to want to stick around to do the same!

Ian had already picked out Lucky Belly for lunch, a much raved-about ramen restaurant that’s very much part of the trendy food movement happening in Chinatown right now. If you’ve opened a food or travel magazine in the last few years and read about a bar or restaurant on Oahu, it’s likely that it was in these surrounding blocks.

We sat at the bar and I went for the oriental chicken salad with mandarin oranges & sesame dressing while Ian went for a signature ramen bowl — we were both delighted.

After, we walked off lunch with a bit of window shopping — which was dangerously close to becoming real shopping — at boutiques like Owens and Co. and Ginger13.

Heading back to Waikiki to freshen up for the evening, I convinced Ian to swing through the government district of Downtown. While I didn’t really have an interest in touring the stuffy interiors, I wanted to stand in front of ʻIolani Palace, and poke around the court house and post office, where I’d heard a rumor there was a beautiful grove of Banyan Trees in the parking lot.

It was a worth-while stop on both fronts.

The Banyan trees were no joke. I loved that this beautiful grove was hidden in a municipal parking lot, preserved with love as a city sprung up around them.

the couple that wears flamingos together, stays together

Later that evening, after a recharge back at our cute hotel, we hit Chinatown again for the First Friday Art Walk. I’d raved to Ian about my previous experience with Chinatown’s Art After Dark, which takes place the last Friday of every month, and was excited to check out its first-week-of-the-month counterpart.

We kicked things off with The ARTS at Marks Garage, where we had a glass of wine, listened to live music, checked out the photography exhibit on display and mingled with Oahu’s art-erati.

Next, we popped around the corner to the Pegge Hopper Gallery, where I fell so in love with the paintings that I bought a print that I hope I’ll get the chance to hang somewhere, someday.

Now, walking around Chinatown at night is something that will probably raise eyebrows in certain circles. It’s true that this is one of Oahu’s seedy areas and it’s kind of ground zero right now for the island’s controversial battle against homelessness. Critics claim the government is criminalizing poverty in order to maintain a shiny, smiling version of Waikiki to visitors, while proponents point to data showing that it’s the number one issue that dissuade tourists from returning to Hawaii (if anything dissuades them at all).

I admit I am fascinated by this complex issue and have read extensively up on it as a result. Still, I was surprised when Ian briefly leaned against a wall while I was consulting my phone for directions and a security guard rushed over to tell him doing so was illegal! Barring people from sitting down or even leaning on public buildings and roads is one of the ways lawmakers have tried to flush the homeless population out of areas visible to tourists.

Still, Chinatown is, for the moment, home to a very large population of people without traditional homes, so be aware that this isn’t the Disney-sanitized version of Hawaii and you’ll likely step around someone’s makeshift tent once or twice while visiting this area. Violent crime is rare but petty theft does occur — while we felt 100% safe walking around during the day, we did try to avoid flashing my phone and camera around and night and stick to the busier main streets as opposed to random dark alleys.

But wandering around had its rewards — while walking by the Hawaii Theater, we stumbled on an impromptu capoiera circle that we briefly gathered to cheer around.

We made a few more stops — including TEN41 Studios + Gallery, which was a bit out of the way so had smaller crowds but super friendly, engaging artists, and the Chinatown Artists Lofts, where over a dozen small studios looked over a courtyard with live music, food stalls, and a small bar.

There are maps on the First Fridays website, but we were pretty happy just wandering around and asking for suggestions for where to go next at each stop.

Buzzing with creative energy, we made our way over to The Pig and The Lady, arguably one of the hottest reservations in town. The interior design, the plating, and the menu were swoon-worthy, and I could see why foodies from as far away as the mainland were buzzing over this place.

Ian, needless to say, was in heaven.

After dinner, we attempted to hit some of the hip bars on Hotel Street, but we were shocked to find lines snaking around the corner! It had been a ghost town when we were on our way in. One of the bouncers tipped us off that First Friday is the night for local university students to hit Chinatown — it’s literally the busiest night of the month. Oops. Insider tip, gleaned from experience — before you go to your dinner reservation, hit the bars you want to go to after and get your hand stamped.

You really can’t go wrong with any of the bars on that stretch, but our favorite is Smith’s Union Bar, the oldest in Oahu, and a total dive where you can get cheap drinks and sit at your seat, get passed a microphone from across the bar, and belt out karaoke for $1 a song. After elbowing our way to the bar a few times, we called it a night.

When Ian and I daydream about that big lottery win someday (which, frankly, is going to be pretty hard to score considering neither of us buys lottery tickets), we already have Oahu all planned out — a slick studio in Chinatown or Kakaako for the weekends, and an old ramshackle house on North Shore for the rest of the week.

I know among my hardcore travel friends, Oahu often gets overlooked in favor of its sister islands, but we are just plain obsessed with Oahu — and Chinatown is a big part of that. If you’re staying in Waikiki, it’s an easy public bus ride from Oahu or a short thirty minute drive away. Don’t miss it! Maybe someday I’ll get to wave to you from my window.

Next up? Over to the island of Maui!

Mahalo to Carter for hosting us on our Honolulu Exposed tour!

Confused on where we are? I’m catching up on the black hole of content from August of 2016 to April of 2017 — when I jumped forward to blog the summer of 2017 as it was happening. Right now, we’re in October of 2016 in Hawaii, and I can’t wait to turn my detailed notes and journals into blog posts from Jamaica, Thailand and Bali next! My apologies for any confusion with the timeline, and thanks for sticking with me.

Wow! Love love love the sound of that tour & these neighbourhoods. When my Hawaii dreams finally come true, I would love to take the Queen Lili`uokalani tour. Been fascinated by her & pre-American Hawaii since I read her autobiography some years ago!

This side of Oahu looks incredible! I was there last year visiting a friend who was stationed there with the military so we spent a lot of our time on the east part of the island, but now I’m wishing she still lived there so I could check out more of Honolulu! We just did a quick stop in Waikiki to check it out and that was about it in terms of city stuff.

I love that you included some of the lesser known history and locations of Oahu.
That seems like such an interesting tour that I’d love to check out if I even find myself back!
And I’m right with you for wanting a house on the North shore, I went with my family a few years ago and my parents rented a house right on the beach on the North shore, it was one of my favourite trips I’ve ever taken! I still dream of moving there some day. Although I’m not American so I’ll definitely need that lottery win haha!

So by Downtown do you mean Honolulu’s downtown? Or is there a separate area called Downtown? I love how that tour you took showed how people in Hawaii’s past and present are just people like everyone else

Yeah, Honolulu’s Downtown. I actually was trying to research while writing this post if Chinatown is considered a part of Downtown or if they are separate entities within Honolulu, but couldn’t really get a clear answer (I THINK that Chinatown is a portion of Downtown, which is part of Honolulu along with Waikiki, Ala Moana, Kakaako and others.) I’ll need to clear it all with a cartographer, eventually, ha ha.

I put Carter’s tours right on my list! I love a tour that’s a bit different than just the main sights. Getting to know the gritty details of an area are so much more fun than some of the more “plain” highlightsDominique recently posted..Havana’s Best Kept Secret – Fusterlandia

Hi Alex,
I have been following your blog for quite a while and love it. At this point I feel you are a pro at traveling in Thailand. My sister and I are spending a month in Koh Samui and like it so much we would like to come back for longer next year. Can we stay for 90 days or do we have to get off the island after 60?
Thanks,
Carol

Hey Carol! What country are you from? You’ll need to apply for a tourist visa in your home country (assuming you can) and then after sixty days (well, like a week before) go to the immigration office in Mae Nam and get a thirty day extension. So as long as you get that visa at home, you won’t have to leave the island for ninety days!

Alex,
Thanks so much – you have made my day. I am living in Western Massachusetts. We had written to the Thai office in Boston, but had not heard back and wanted to plan for next year while we are on the Island. Again, thanks,
Carol

I'm a New York native who left my home to explore the world slowly and thoroughly. I’m just a little obsessed with photography, scuba diving, and reading guidebooks to countries I have no immediate plans to visit.